4.alpha.,6-Dihydroxy-5-iodo-2.beta .-aryloxymethyl-3.alpha.-tetrahydropyranoacetic acid .gamma.-lactone, 6-alkyl ethers

- The Upjohn Company

The present specification provides novel intermediates and novel processes for the synthesis of Thromboxane B.sub.2 (11a-homo-11a-oxa-PGF.sub.2.sub..alpha.), its 15-epimer, and various carboxyl derivatives thereof. In particular, there are disclosed various bicyclic tetrahydropyran-containing lactones useful in the above processes, and corresponding acyclic lactones.

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Description

The present invention relates to thromboxane B.sub.2 and associated intermediates and processes for which the essential material constituting a disclosure therefor is incorporated by reference here from Ser. No. 676,890, filed Apr. 14, 1976, now pending issuance as a United States Patent.

Claims

1. A thromboxane intermediate of the formula ##STR1## wherein R.sub.34 is an arylmethyl hydroxy-hydrogen replacing group selected from the group consisting of

(a) benzyl,
(b) benzyl substituted by one to five alkyl of one to four carbon atoms, inclusive, chloro, bromo, iodo, fluoro, nitro, phenylalkyl of 7 to 12 carbon atoms, inclusive,
(c) benzhydryl,
(d) benzhydryl substituted by one to ten alkyl of one to four carbon atoms, inclusive, chloro, bromo, iodo, fluoro, nitro, phenylalkyl to 7 to 12 carbon atoms, inclusive,
(e) trityl, and
(f) trityl substituted by one to 15 alkyl of one to four carbon atoms, inclusive, chloro, bromo, iodo, fluoro, nitro, phenylalkyl of 7 to 12 carbon atoms, inclusive;
And wherein R.sub.33 is alkyl of one to 5 carbon atoms, inclusive.

2. 6.alpha.- OR 6.beta.-METHOXY-5.beta.-IODO-4.alpha.-HYDROXY-2.beta.-BENZYLOXYMETHYL-3.al pha.-TETRAHYDROFURAN ACETIC ACID,.gamma.-LACTONE, A THROMBOXANE INTERMEDIATE ACCORDING TO CLAIM 1.

Referenced Cited
U.S. Patent Documents
3806540 April 1974 Martel
Patent History
Patent number: 4032542
Type: Grant
Filed: Apr 14, 1976
Date of Patent: Jun 28, 1977
Assignee: The Upjohn Company (Kalamazoo, MI)
Inventor: Robert C. Kelly (Kalamazoo, MI)
Primary Examiner: Cecilia M. Jaisle
Attorney: Robert A. Armitage
Application Number: 5/676,895
Classifications
Current U.S. Class: 260/3436; 260/343; 260/3433R; 260/3435; 260/3457; 260/3458; 260/395; 260/468D; 260/479S; 260/483; 260/514D; 260/535R; 424/283
International Classification: C07D49304;